One Of Illinois' Best Fall Escapes Is A Dreamy Wine Trail With Vibrant Foliage And Charming Local Destinations

Autumn is a magical time, when the air crisps, leaves turn, and coziness begins. From the best pumpkin patches in America to breathtaking destinations with stunning fall foliage and cozy stays, there are plenty of reasons to get outdoors before winter. One of the best Midwest fall escapes is the Shawnee Hills Wine Trail, a dreamy, 45-mile meander through rural roads, vineyards, and tasting rooms across small towns in southern Illinois. The trail is backdropped by the Shawnee National Forest, a stunning scenic wilderness where sumac, sweetgum, sassafras, and maple trees blaze hues of crimson, orange, and gold in October.

The Shawnee Hills Wine Trail was established in 1995 by owners of the region's original three wineries to promote local tourism. Illinois isn't widely known for wine — California's Tuscan-like hills in Napa or Sonoma County usually steal that spotlight — but the Shawnee Hills Wine Trail now includes a dozen wineries across three counties (Union, Jackson, and Williamson), all part of the Shawnee Hills American Viticultural Area (AVA), a well-regarded region located between the Ohio and Mississippi Rivers. The area boasts pre-glacial limestone, thin soil, and a high elevation, which, along with a warm climate, allows a lengthy growing season and higher grape sugar content. Sugar is what transforms into alcohol, giving these Shawnee Hills wines a higher ABV. Chambourcin, chardonnay, cabernet franc, traminette, and vignoles are among the region's top grape varietals.

Even if you're not an oenophile, there's plenty to do here, including hiking, camping, biking, zip-lining, great restaurants, shops, boating, and fishing. And if you prefer hops over grapes, the Southern Illinois beer trail loosely overlaps with the wine-forward route — one of the wineries even brews its own beer! So pack your sweaters and boots and get ready for autumnal magic in this underrated Midwest wine region.

If you're after a quick fall getaway, you can pack plenty into two days on the Shawnee Hills Wine Trail. If you're planning to drink, consider booking a local shuttle. Wrightway Transportation offers custom tours, while Shawnee Shuttles run seven-hour itineraries and can help coordinate accommodations.

Start in Alto Pass on the west side of the trail. Alto Vineyards, the area's first winery, was founded in 1988 by an Italian winemaker and now serves award-winning wines in a relaxed, scenic setting. Nearby, Pomona Winery offers non-grape, fruit-forward wines, utilizing apples and berries, and Hickory Ridge, a family-owned and operated vineyard, exclusively uses estate-grown grapes, offering a unique regional taste. The scenic Kite Hill Vineyards is in the nearby Carbondale, a laidback college city featuring lakeside fun, where you can also grab a coffee or check out an art gallery. Head down State Route 127 from Kite Hill until you get to Von Jakob Winery and Brewery, the only stop on the trail that makes its own beer and has a distillery. It features eight signature small-batch beers and rotating seasonals. Have a flight and spend the night at the vineyard's charming bed-and-breakfast, or head back toward Alto Pass to stay at the historic Havisham House, a beautifully restored 1892 B&B often used for weddings.

Of course, no Midwest fall getaway is complete without a visit to an apple orchard or pumpkin patch — and the Shawnee Hills region delivers. Stop by Rendleman Orchards for pre-picked fresh apples, pumpkins, a butterfly and bird sanctuary, and pillowy apple cider donuts. Just down the road, Flamm Orchards, known for its summer peaches and fall apple harvests, also serves up fresh-baked seasonal treats and farm market goods.

After all that, you've still got several wineries left. Blue Sky Vineyard is a Tuscan-style winery with charming Italian vibes, and StarView Vineyards serves excellent dry wines beside a small lake, with live music on weekends. Honker Hill is known for its relaxing vibe — try the villard blanc for a citrusy taste — while Feather Hills has quality food and vineyard tours. One of the smallest wineries is Wichmann Vineyard, founded by the daughter of one of the wine trail's original founders, Ted Wichmann of Owl Creek (which is also a noteworthy stop for its craft wine and hard ciders on the trail's east side).

The region takes its name from the Shawnee Hills tribes who once lived here. The infamous Trail of Tears also cuts through the Shawnee National Forest, wherein the U.S. government forced Native Cherokees west. You can retrace a 1-mile portion of the trek at Hamburg Hill. Meanwhile, Anna, just south of wineries like Owl Creek and StarView, is near a historic Cherokee cemetery and is home to the site of the historic third Lincoln-Douglas Debate. These sites add a sobering but meaningful layer of history to the region's cultural richness and are worth the detour. 

Squeeze in a hike at the Little Grand Canyon in Shawnee National Forest or visit the nearby Giant City State Park. The Tunnel Hill State Trail is also a haven for cyclists, though it's not easily accessible to the wineries. You can also cast a line at Cedar Lake, but note that the beaches close after Labor Day. Don't miss the Shawnee Bluffs Canopy Tour, an 83-acre, eight-line zipline playground that will really give you a chance to see fall colors.